There are a number of characters in Sherwood Anderson'sWinesburg, Ohio. As there are several parts, you will want to thoroughly read eNotes' character descriptions, but here are a few:
In the middle of the book, there is a story presented in four parts called "Godliness." The main character is Jesse Bentley—when his brothers are killed in the Civil War, although Jesse wanted to be a minister, he inherited the family farm and ends up being very successful with it.
In the part called "Hands," Wing Biddlebaum is a rather mysterious character. The town knows very little about him. It is easy to understand why: accused of lewd behavior with one of the boys in his class, he was all but tarred and feathered in the town he has come from, and he doesn't speak of it.
Then there are the Willards: George (who is the major—"central"—character of the book) is a reporter for the paper and gets to know many of the people who come to or pass through town; Elizabeth, George's mother, who suffers from depression and is a very unhappy woman; and, Tom Willard is George's father who married his mom when she became pregnant—he's not very good at keeping up the boarding house.
Belle Carpenter hangs around with George Willard, but they are not seriously dating; she is in love with someone else.
Curtis Hartman is a pastor (minister) in "The Strength of God." His faith is being tested, and he finds himself much too interested in the woman living in the building next to his office whose name is Kate Swift. She is a teacher—George's former teacher, in fact.
Dr. Parcival is not a doctor, but pretends to be one in "The Philosopher." This is not the first time he has pretended to be something he is not.
Dr. Reefy actually is a doctor. He is in two of the stories and is connected to Elizabeth, George Willard's mom.
Seth Richmond is a friend of George's. They are similar to each other, though Seth probably is not as secure as George. Their father's have a similar history of failed parenting and providing for family, but Seth's father is dead.
Enoch Robinson is also insecure and is particularly paranoid. He is sure the town is making fun of him and his family.
Louise Trunion and George have a "one night stand." They don't have a relationship, and their time spent together leaves George particularly unhappy.
Joe Welling is "A Man of Ideas." He falls in love with Sarah King and fears that the men in her family might harm him, but surprisingly, they seem to enjoy his company.
Helen White and George have a connection. And while it might seem that it is physical, it is not. It is more a connection that allows each to get back in touch with his/her inner child, and they enjoy eachother's company. As people, they have a great deal in common, but it is not romance.
Wash Williams is a friend of George's. The reader learns that his wife cheated on him, ending their marriage.